4-tert-butyl 1-(2''-cyanoethyl) 2-(5'-tert-butoxycarbonylaminopentyl)-but-2-Z-enedioate | 808134-29-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-tert-butyl 1-(2''-cyanoethyl) 2-(5'-tert-butoxycarbonylaminopentyl)-but-2-Z-enedioate
• 英文别名: 4-O-tert-butyl 1-O-(2-cyanoethyl) (Z)-2-[5-[(2-methylpropan-2-yl)oxycarbonylamino]pentyl]but-2-enedioate
• CAS: 808134-29-4
• 化学式: C₂₁H₃₄N₂O₆
• 分子量: 410.511
• InChiKey: JHRGMPSIGIHWJC-NXVVXOECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-tert-butyl 1-(2''-cyanoethyl) 2-(5'-tert-butoxycarbonylaminopentyl)-but-2-Z-enedioate 在 盐酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 4-(tert-butyl) 1-(2-cyanoethyl) 2-(5-(2-(3-((3aS,4R,6R,7S,7aS)-7-((((9H-fluoren-9-yl)methoxy)carbonyl)oxy)-4-(((((9H-fluoren-9-yl)methoxy)carbonyl)oxy)methyl)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)propanamido)acetamido)pentyl)maleate
  参考文献：
  名称：

  Facile Preparation of an Orthogonally Protected, pH-Sensitive, Bioconjugate Linker for Therapeutic Applications

  摘要：

  We describe the facile, three-step synthesis of an orthogonally protected, pH-sensitive linker (8), based on maleic acid, and report its application to the preparation of a pH-sensitive phospholipid (20) for potential use in drug and gene delivery. In addition, we highlight the benefits of our linker over the use of the commercially available cis-aconitic anhydride (4).

  DOI：

  10.1021/ol0483347
• 作为产物：
  描述：

  N-tert-butoxycarbonyl-8-amino-3-oxo-2-(triphenyl-λ⁵-phosphoranylidene)-octanenitrile 在 氧气 、 sodium hydride 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.58h， 生成 4-tert-butyl 1-(2''-cyanoethyl) 2-(5'-tert-butoxycarbonylaminopentyl)-but-2-Z-enedioate
  参考文献：
  名称：

  Facile Preparation of an Orthogonally Protected, pH-Sensitive, Bioconjugate Linker for Therapeutic Applications

  摘要：

  We describe the facile, three-step synthesis of an orthogonally protected, pH-sensitive linker (8), based on maleic acid, and report its application to the preparation of a pH-sensitive phospholipid (20) for potential use in drug and gene delivery. In addition, we highlight the benefits of our linker over the use of the commercially available cis-aconitic anhydride (4).

  DOI：

  10.1021/ol0483347

文献信息

• Facile Preparation of an Orthogonally Protected, pH-Sensitive, Bioconjugate Linker for Therapeutic Applications
  作者：Steven Fletcher、Michael R. Jorgensen、Andrew D. Miller

  DOI：10.1021/ol0483347

  日期：2004.11.1

  We describe the facile, three-step synthesis of an orthogonally protected, pH-sensitive linker (8), based on maleic acid, and report its application to the preparation of a pH-sensitive phospholipid (20) for potential use in drug and gene delivery. In addition, we highlight the benefits of our linker over the use of the commercially available cis-aconitic anhydride (4).